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For intermolecular diastereoselective alkyl additions to the iminic carbon in related molecules, see
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For reviews, see
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For our previous asymmetric syntheses of 2,2-difluoro-1-ACACs, see
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For our previous asymmetric syntheses of 2,2-difluoro-1-ACACs, see
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Imino lactones 4a, b were prepared by condensation of the corresponding α-keto esters with (R)-phenylglycinol; see ref 3a
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Imino lactones 4a, b were prepared by condensation of the corresponding α-keto esters with (R)-phenylglycinol; see ref 3a.
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26
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77954114643
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The pure cis isomer of 5a was also obtained by a different synthetic route based on the partial hydrogenation of a triple bond, and its subsequent cyclization to 6a afforded the same stereochemical result as the trans / cis mixture
-
The pure cis isomer of 5a was also obtained by a different synthetic route based on the partial hydrogenation of a triple bond, and its subsequent cyclization to 6a afforded the same stereochemical result as the trans / cis mixture.
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27
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77954102718
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The diastereomeric ratio was measured by HPLC. Only three out of four diastereoisomers were detected both by HPLC and NMR
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The diastereomeric ratio was measured by HPLC. Only three out of four diastereoisomers were detected both by HPLC and NMR.
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N -Allylation of 6a was also tested but resulted in a complex mixture of products under several reaction conditions
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N -Allylation of 6a was also tested but resulted in a complex mixture of products under several reaction conditions.
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Cis -fused 2-azabicyclo[4.3.0]nonane-1-carboxylic acids were previously prepared and used as scaffolds for β-turn mimics, see
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Cis -fused 2-azabicyclo[4.3.0]nonane-1-carboxylic acids were previously prepared and used as scaffolds for β-turn mimics, see
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For a recent article combining both iminium ion additions and gold-catalyzed hydroaminations, see
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In contrast, a similar hydroamination protocol was unsuccessful using vinylic derivative 6a
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In contrast, a similar hydroamination protocol was unsuccessful using vinylic derivative 6a.
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